The 5E ROGUE

The rogue in 5th Edition D&D is excellent to put it simply. No longer are you a skill monkey who at best is difficult to effectively apply in combat and at worst the guy stuck in the back with a thumb up their rear end waiting for the fight to be over. In previous editions of D&D you were playing the rogue like a pro if you commonly achieved a sneak attack. In 5E if you have failed to get a sneak attack each round then the fault lies entirely on you. You are the subject matter expert, providing utility out of combat and precision strikes in the flurry of combat.

The class stands on its own well, and supplemented with a bit of multi-classing can provide some truly unique play styles and capabilities. The objective of this guide will be to give an overview of what rogues characteristically should be looking for in 5th edition during character creation, and go on to provide optimized sample builds. In short, if you are looking to play a character that makes use of clever tactics in combat, is able to dish out respectable damage, and still provide great utility for yourself and the party outside of combat, a rogue build is for you.

First it should be made clear that because of how well D&D 5E is balanced as a whole, a player actually needs to sort of go out of their way to create a “bad” character build. While it can be objectively stated that certain character aspects of the rogue are more important than others, by no means should seeing a stat or feature rated poorly in this guide lead you to believe that it is out of the question.

Assumptions

• You are playing a rogue because you are willing to trade combat effectiveness for out of combat utility. You will be outclassed in damage by any well-built fighter, and this is why several rogue builds in this guide will dip into fighter, but that is what you pay to have some great out of combat fun, and your role in combat will be extremely rewarding when successfully operated.

• This guide focuses the rogue's out of combat utility on being able to win friends, influence npc’s, ferret out information, perceive threats before they happen, and find hidden aspects of the world. You can be the party face, or team up with the bard and get involved in deep shenanigans. There are a multitude of other opportunities for utility as well and you should go search for them yourself.

• Combat will be played on the tabletop with a grid. Many of the rogue’s combat abilities center on positioning around the board to optimize your impact, and playing everything in the theater of the mind can make playing an effective combat role difficult for the rogue. If you still want to play the rogue, it is suggested by this guide to build a complete skill monkey and leave combat to the fighters if this is the case.

• Your Dungeon Master (DM) allows for all the races included in the players handbook (PHB), character customization options outlined in Chapter 6 of the PHB, as well as the rules for creating custom backgrounds outlined at the beginning of the backgrounds section. Most rogue builds rely on feats and multi-classing to achieve full potential. You may want to consider playing with a different group if this is the case, as this can also be a red flag that the DM likes to strangle creativity, but your mileage may vary.

• You as a player have a basic understanding of the PHB. If you don't recognize or are confused by something in this guide, the PHB should have the answer/clarification.

• This guide only considers the options presented by the core rulebooks and the sword coast adventurer’s guide. As usual feel free to ask your DM about homebrew stuff, but this guide aims to cater to a wider audience.

Questions for your DM

• Will you be using the Optional Rule: Flanking as per the Dungeon Master's Guide (DMG), or a homebrew variant of it? This rule is massive for melee rogues and you should strongly consider it over ranged builds if this rule will be used. Some might even argue it’s overpowered because as long as your party’s tank works with you a little bit you both can basically deal out two-man advantage take down’s like nobody’s business. Then again, so could your foes. That opinion is all up to your DM… but you should ask. Don’t whine about it if they don’t use it; a whiny rogue is the quickest way to make your DM dislike you, and rightfully so.

• Ensure your DM understands that the rogue in 5E is balanced around getting a sneak attack every round in combat. This does not mean that you deserve a sneak attack every round, but that you should be able to find an opportunity for one far more commonly than previous editions. A quick comparison to simple fighter builds should illustrate how the fighter will quickly out damage the rogue every turn even assuming the rogue always gets a sneak attack. Don't be bullied into losing a sneak attack when the rules as written (RAW) say you should.

• Will you be paying close attention to illumination? This guide assumes so, and as such stresses the importance of the Darkvision racial trait, but it the DM treats this casually, then suddenly races without it become much more viable.

TL;DR

Don’t be put off by the rogue if you are a new player. If you enjoy game grid tactics and outsmarting your foes the rogue is the class for you. Let’s get started.

Stats

Ability Scores are the center of any build. The table below shows which key character aspects and skills are related to each of the 6 Ability Scores.

Ability Scores

Ability	Benefits
Strength	Athletics
Dexterity	Attack Bonus, Damage, AC, Initiative, Dexterity Saves, Acrobatics, Sleight of Hand, Stealth
Constitution	Constitution Saves, Health Points
Intelligence	Arcana, History, Investigation, Nature, Religion
Wisdom	Wisdom Saves, Animal Handling, Insight, Medicine, Perception, Survival
Charisma	Deception, Intimidation, Performance, Persuasion

Under standard point buy you will have a 15, 14, 13, 12, 10, and 8 score to use, where of course you can move the points around provided that no score is higher than 15 or lower than 8. Remember that point buy is not linear and that moving to higher numbers past 13 start costing 2 points instead of 1. Depending on your race you will have between 2 and 6 points to add to certain ability scores. As you know only even scores matter, so a good goal to have would be to start the game with only even scores.

Combat Method

In choosing Ability Scores your first question should be, how will you do damage? For the rogue that is done with physical weapons that are finesse or range based because those are the only methods that allow you to apply the rogue's sneak attack damage. This means no damage spells, and no big clunky weapons. Therefore, Strength is your dump stat, and Dexterity needs to be as high as possible to start. Strength based rogue builds are possible, but usually once you get done building one you realize you should have just played a heavy duty fighter.

Lacking Athletics means that you will not be optimized for combat actions that use it, climbing, or swimming. This can be disappointing at times. The rebuttal to this is that you should simply avoid doing these things, and that Acrobatics can sometimes be used in place of Athletics if your DM agrees that it makes sense, for instance: some climbing scenarios. Also, there are a variety of ways to obtain bonuses to climbing and swimming checks specifically.

Dexterity Skills

Skill	Rational
Acrobatics	You are a dexterity based combat artist. Get creative and this will reward you. Although 5E has simplified combat and thus it arguably has less utility, it still has a high skill ceiling.
Sleight of Hand	This can be useful for more than just pick-pocketing. Think outside the box.
Stealth	You don’t have to take this, but you don’t have to play the rogue either.

Utility Choice

Which type of character do you want to roleplay, or to be more direct, what type of utility will you bring to the party? The biggest reason to play the rogue is to fill a utility role that the part lacks, and be really damn good at it. There are three major directions, and each one is based off a different ability score.

Most Rogue's will find themselves wanting to pick and choose between these three utility categories. This can be a little difficult when there are not enough Ability Points to go around, but there is something to be said for having a varied skill set even at lower modifiers. Your race will have a big impact on whether you should focus on a certain set, or spread them out, but ultimately it all depends on what the party needs and what you want to roleplay.

Party Face (Charisma)

Skill	Rational
Deception	Fooling people is a big part of the Persuasion effort. Swap for intimidation if that is your style; you don’t need both.
Intimidation	Take this if you like the idea of scaring people to do what you want. Does the same job as deception most times, but having both can be helpful as one will be better depending on the situation.
Performance	In the rogues eye's this could be to create a distraction or alter the mood of a crowd. However, a Bard can do it better, and you don't want to be the distraction, but the one benefiting from it.
Persuasion	The skill to let you win friends and influence people. When you are not in combat this is what you do. A true must have if you go this route.

Often the best choice is to be the party face, the people person who has high Charisma and is able to talk the party out of a tense situation. It is a great option because the Rogue will be the best possible choice for this role thanks to the Expertise ability. Deception and Persuasion are the must have skills. This role will be challenged by Bards, Paladins, Sorcerer's, and Warlocks as Charisma is tied to their casting ability. If your party has one, they should do this job, and you move on to the next possibility.

Wizened Warrior (Wisdom)

Skill	Rational
Animal Handling	The ranger class is just a couple pages back. This skill is fairly useless to any rogue.
Insight	Being able to tell if the party is being lied to is just as important as being able to persuade people to do what the party wants.
Medicine	Unless you don’t have a healer in the party you don’t need this. It is never bad to have though.
Perception	The skill of “letting you detect the presence of something.” Easily the most rolled skill in the game, and incredibly important for helping you avoid trouble.
Survival	Again, the ranger class is just a few pages back. Unless you are going for a certain backstory just leave it be. If your party needs this gap filled just take the Outlander Backstory Wanderer feature and you will be set well enough.

The second choice is the wizened warrior, the one with high Wisdom and can help the party survive harsh environments, spot the little details, and tell when the party is being lied too. The must have skills are Insight and Perception. This role will be challenged by Clerics, Druids, and Rangers, as this is their primary casting ability.

The Bookworm (Intelligence)

Skill	Rational
Arcana	The world of D&D is filled with magic, and somebody in the party needs to do this. If your party has a caster, then they will be better at this than you.
History	Knowing is half the battle, and knowledge in History can grant your party some useful quest information.
Investigation	Finding traps, looting rooms, observing hidden facets to dungeons, scouring the town for information, etc. All classic jobs where the party looks to the Rogue.
Nature	Knowing is half the battle, and knowledge of the environment you are going to be exploring can save the party more than just keeping their boots clean.
Religion	The world of D&D is rich with religions, and knowing them can help prevent party faux pas which lead to an angry room ready to fight you. Take note though that many DM's will not strongly incorporate Relgion into their world, while Arcana, History, and Nature have guaranteed use in a variety of aspects.

The third choice is to be the bookworm, the one with high intelligence, able to scour an area for information and recall related information about the world when necessary. The must have skill is Investigation. This role will be contested by Wizards, which you should be hopeful of. Intelligence used to be a big thing for Rogues, but now its usefulness is far more limited. Being able to find traps is great, but your real job is disarming/dealing with the traps. You don't have to be the dedicated trap spotter so to say.

Optimal Races

Ability scores are the biggest defining factor when choosing a race, and all of these races have those fitting a rogue, as well as skill priority and features to supplement the rogue nature.

Human

Category	Bonus
Ability Scores	+1 to all Ability Scores
Speed	30ft
Languages	Common & 1 extra

The standard human is fine for any build, and is used as a means of comparison to the other races. Think of Ability Scores as currency when considering race. The Human has 6 extra total. Unfortunately one of them is forced into your dump stat, and honestly you should ask your DM if you could spend them freely instead of being restricted to one in each ability score. Standard the Human can get 16, 16, 14, 12, 10, 09. The Half Elf can get the same stats and extra abilities.

Half Elf

Category	Bonus
Ability Scores	+2 Charisma, +1 to two Ability scores
Skills	+2 skill proficiencies
Speed	30ft
Languages	Elven, Common, +1 extra
Special Abilities	Darkvision, Fey Ancestry

The Half Elf is hands down the best go to race for the Rogue. You rarely want to dump Charisma, you tie the Human for the highest ability score stat line, and you get 2 extra skills, 2 good abilities, and another language, all for a net loss of 2 ability points, one of which is taken from the dump stat, the other from shifting point buy numbers around.

Wood Elf

Category	Bonus
Ability Scores	+2 Dexterity, +1 Wisdom
Skills	Perception
Speed	35ft
Weapon Proficiencies	longsword, shortsword, shortbow, and longbow
Languages	Elven & Common
Special Abilities	Darkvision, Fey Ancestry, Trance, Mask of the Wild

The Wood Elf spends 3 ability points for 1 skill, extra movement, Darkvision, Fey Ancestry, Trance, Mask of the Wild, and Weapon Proficiencies. This trade is justifiable if you want to play an Assassin with the ability to hide in minimal cover, start with a longbow, use Darkvision to take up advanced positions and have extra speed to help you in a pinch. The Wood Elf does suffer from having an odd ability score, but this can be fixed by taking the Observant Feat.

High Elf

Category	Bonus
Ability Scores	+2 Dexterity, +1 Intelligence
Skills	Perception
Speed	30ft
Weapon Proficiencies	longsword, shortsword, shortbow, and longbow
Languages	Elven, Common, +1 Bonus Language
Special Abilities	Darkvision, Fey Ancestry, Trance, +1 Wizard Cantrip

The High Elf spends 3 ability points for 1 skill, Darkvision, Fey Ancestry, Trance, a Wizard Cantrip, Weapon Proficiencies, and a language. This is justifiable for an Arcane Trickster or Mastermind archetype build. The Cantrip can give you extra flexibility and both of these archetypes benefit from high intelligence. Again, the Observant Feat can help level out your odd ability score.

Lightfoot Halfling

Category	Bonus
Ability Scores	+2 Dexterity, +1 Charisma
Speed	25ft
Languages	Halfling & Common
Special Abilities	Lucky, Brave, Halfling Nimbleness, Naturally Stealthy

The Lightfoot Halfling spends 3 ability points and movement for Lucky, Brave, Halfling Nimbleness, and Naturally Stealthy. This is only justifiable for those who want to play a Halfling for roleplaying reason's, are committed to a ranged build, and intend to make full use of Naturally Stealthy for cheesy sneak attack setups which many DM's will not be happy with. Again, the Observant Feat can help level out your odd ability score.

Variant Human

Category	Bonus
Ability Scores	+1 to two Ability Scores
Skills	1 skill
Speed	30ft
Languages	Common & 1 extra
Special Abilities	1 Feat

The Variant Human pays the highest price, spending 4 ability points for 1 skill and 1 Feat. On the basis alone that 2 ability points are equivalent to 1 feat it is immediately clear why this Variant Human is a short sighted choice. While it is true that by taking certain combat feats you will be very powerful in levels 1-3, after that you are behind every other race for the rest of the game. Some DM's ban the Variant Human for this very reason, as it is bad for their early game balance, and it is bad for you later on. To get the most out of playing a Variant Human you should play a fighter anyway.

Backgrounds

As per the PHB pg. 125, you may customize any background with two skills, two tool proficiencies or languages, and one background feature. Skills have already been covered, so this section only need mention tools & background features that are good for Rogues. Ultimately just take the tools you want to help you with your roleplaying and read the background descriptions to help yourself form your own backstory for how you want to play outside of combat.

Charlatan

Feature: False Identity

You have a second identity which you can assume, & you can forge documents provided you have seen an example of what you attempt to forge.

Courtier

Feature: Court Functionary

Your knowledge of how bureaucracies function lets you gain access to the records and inner workings of any noble court or government you encounter. You know who the movers and shakers are, whom to go to for the favors you seek, and what the current intrigues of interest in the group are.

Criminal / Spy

Feature: Criminal / Spy Contact

You have a reliable and trustworthy contact who acts as your liaison to a network of other criminals / spies. You know how to get messages to and from your contact, even over great distances, and know the local people who could deliver such messages.

Far Traveler

Feature: All Eyes On You

Your accent, mannerisms, figures of speech, and perhaps even your appearance all mark you as foreign. Curious glances are directed your way wherever you go, which can be a nuisance, but you also gain the friendly interest of scholars and others intrigued by far-off lands, to say nothing of everyday folk who are eager to hear stories of your homeland. You can parley this attention into access to people and places you might not otherwise have, for you and your traveling companions. Noble lords, scholars, and merchant princes, to name a few, might be interested in hearing about your distant homeland and people.

Guild Artisan

Feature: Guild Business

Choose a guild and work with the DM to establish it in the world. You know the skills needed to created finished items pertaining to your guild from raw materials, as well as trade principles and business practices.

Outlander

Feature: Wanderer

You have an excellent memory for maps and geography, and you can always recall terrain layouts, settlements, and other map features. Additionally, you can find food & fresh water for up to 5 people each day provided the land offers it in some way.

Urban Bounty Hunter

Feature: Ear to the Ground

You are in frequent contact with people in the segment of society that your chosen quarries move through. These people might be associated with the criminal underworld, the rough-and-tumble folk of the streets, or members of high society. This connection comes in the form of a contact in any city you visit, a person who provides information about the people and places of the local area.

Urchin

Feature: City Secrets

You know the secret patterns and flow to cities and can find passages through the urban sprawl that others would miss. When you are not in combat, you can guide your party between intercity locations at twice as fast as your speed would normally allow.

Rogue Abilities

Archetypes will be covered later. This page is merely an opinionated viewpoint on the base rogue abilities.

(1st, 6th) Expertise

Choose 2 proficient skills to double proficiency bonus. This is a great way to start the game by being great at two things. Stealth, Perception, and Persuasion are great picks for this to start.

(1st) Sneak Attack

Extra d6 sneak attack damage once per turn which scales with level. Finesse or ranged weapons only. Requires either advantage or an enemy of the target within 5 feet. This is the crucible ability for the rogue's damage output, and the entire next page is dedicated to examining this ability in utmost detail.

(1st) Thieves' Cant

At its most basic this is just a secret thieves language fluff. The best of DM's and players will find ways to make this useful, but for the common player it never sees actual utility. Note, by taking the Mastermind Archetype you can get the ability to determine class levels of an NPC out of combat. You can also get the same ability by taking 7 levels of fighter with the battlemaster archetype. This would tell you if they have any rogue levels, and thus if they are able to speak Thieves' Cant. Otherwise you can just guess and might get lucky some times.

(2nd) Cunning Action

You can Dash, Disengage, or Hide as a bonus action. This is one of the best abilities in the game, the ultimate insurance policy really. Shifting actions to bonus actions plays a huge role in accomplishing more on every turn. Even a two weapon fighter who needs his bonus action for the off hand attack can still make use of this when things start to look bad.

(4th, 8th, 10th, 12th, 16th, 19th) Ability Score

+2 Ability points or +1 Ability point and +1 Feat. You and the fighter get the most feats (6) of all the classes. Psst, taking 12 levels of rogue and 8 levels of fighter gets you 7 total feats. Just saying.

(5th) Uncanny Dodge

When a seen enemy hits you with an attack you may use your reaction to halve the attack's damage against you. To clarify, this means that if your opponent is rolling the d20 to hit you with an attack in any way, you may use this ability as your single reaction per round. This means you may use it against spells that require an attack roll to hit. For instance, if you are targeted by Fire Bolt, you may use this. If you are targeted by Fireball, you may not (your 7th level Evasion ability will help you here). If you are targeted by magic missile, you may not use this either as once again, no attack roll is needed to hit. This is a huge increase to the rogue's survivability, but remember you only get one reaction per round, so if you get swarmed you are still going to be in a world of hurt.

(7th) Evasion

If you are targeted by an effect that allows you to make a dexterity save, you now take zero damage if you succeed, and half the damage if you fail. This is wonderful to have against enemies with area of effect (AOE) damage attacks. Not always applicable, but still great to have in your bag of tricks to keep you alive.

(11th) Reliable Talent

d20 rolls below 10 = 10 for proficient ability checks. No more getting screwed by chance. This is arguably the best skill for the rogue, especially for a dedicated skill monkey build, as being reliable in performing your party role can be anywhere from nice to preventing a total party kill (TPK). Just a note, this is for ability checks. Not saving throws, not attack rolls, just abilities. If you are called upon to make an ability check in combat, say to oppose a grapple, then yeah it works. But it isn't going to help you make a constitution saving throw to prevent Poison Spray.

(14th) Blindsense

You are aware of hidden/invisible creatures within 10ft. Meh. By this level your casters will have spells available that vastly overtake this in utility. Might be nice if you end up on your own to get you out of a pinch, but still pretty weak for a 14th level ability.

(15th) Slippery Mind

You gain proficiency in Wisdom saving throws. This is a good one as nothing can be more frustrating as a rogue than being taken out of a fight because of a failed wisdom save. Now you are proficient in 2 of the 3 big saves (dexterity, constitution, and wisdom).

(18th) Elusive

No attack roll has advantage against you while you are not incapacitated. This looks good on paper, but compared to other 18th level abilities and the spells being thrown around at this level it is pretty weak. Really this an insurance policy you should not need, because if an opponent has advantage against you, that usually means you are at disadvantage, and thus not getting sneak attack, and thus have made a big mistake. But hey, at the end of the day it isn't bad to have.

(20th) Stroke of Luck

If you miss an attack you can change it to a hit. If you fail an ability check you may treat the d20 roll as 20. One use only, regained after short or long rest. Again, not bad, but pretty lackluster compared to other level 20 abilities. It is good for ensuring your Assassin build opening attack goes off, but if you do that build correctly you will already be attacking with a high bonus to the attack roll and be doing so with advantage. Some might even go as far to say that the Lucky feat is better. The only situation where Stroke of Luck would be better is if you had a monumentally low chance to hit, or none at all.

The Art of Sneak Attack

All right, let's start by reading this ability word for word from the PHB. Beginning at 1st level, you know how to strike subtly and exploit a foe's distraction. Once per turn, you can deal an extra 1d6 damage to one creature you hit with an attack if you have advantage on the attack roll. The attack must use a finesse or ranged weapon. You do not need advantage on the attack roll if another enemy of the target is within 5 feet of it, that enemy isn't incapacitated, and you don't have disadvantage on the attack roll. The amount of extra damage increases as you gain levels in this class, as shown in the sneak attack table.

So you get extra 'Sneak Attack' damage if you have advantage or an able bodied friend next to your target and you do not have disadvantage once per turn. Immediately it should be observed that once per turn means that you may obtain extra sneak attack damage not only on your turn, but also on your opponents turn. However, this will only happen if you have a usable reaction option which allows you to make an attack, such as an opportunity attack when an opponent leaves your threat range. Several builds in this guide will focus on this and try to give as many opportunities to achieve this as possible.

Let us also be clear that 'Sneak Attack' does not literally mean an attack that was sneaky. It can represent anything from striking a vital weak spot while a foe is distracted to displaying supreme swordsmanship and making an excellent strike. The rules clearly define when you get it and when you don't. You may not say something like, "I dodge and weave, looking for an opening, and then I strike for a sneak attack," and then apply sneak attack damage to get it. Don't be discouraged from adding fun descriptions to your sneak attacks, but understand that you don't get to have it by describing an action.

Tactics for obtaining sneak attack

• Attack while hidden. This is the go to option for ranged rogue builds to obtain their Sneak Attack. Being hidden grants advantage on an attack, which gives you sneak attack, and Cunning Action allows you to hide as a bonus action. So you just start the fight or get hidden the first round, then all your next rounds consist of starting with an attack, then hiding right? Well, it is not that simple unfortunately. The rules for hiding state that you cannot hide from an enemy that can see you. So first of all you have to have something to hide behind where you are completely hidden from view. Secondly, you can't stay there after revealing yourself with your attack. You need to move to a new hiding location, because the enemy will be watching that spot. If you have some woods to hide in then perfect, you can dance around in the forest continually hiding and shooting, but hiding behind that turned over cart is only going to work once.

• This should be obvious enough, but get a melee buddy! If you and the tank work together well you can dish out mad damage together. The rogue is all about teamwork, both give and take.

• Kite all day. This is less about getting the sneak attack and more about not being denied it. If you get swarmed by multiple enemies you are in a very bad way, and you don't want to go down. Playing the Rogue well is all about managing your distance.

• Have an ally use a Help action against your target within 5 feet. There is no way your allies are going to do this for you because they want to be using their character's cool abilities, not spending the help action every turn on the their Rogue. So get a Familiar, Conjured creature, or trained animal to do this if you want to use this method reliably.

• Expend Inspiration on your attack.

• Attack a creature that is squeezing through a smaller space (PHB pg 192)

• Attack while you are invisible or otherwise unseen (not required to be hidden).

• Attack a target that is Prone within 5 ft, affected by Faerie Fire, affected by Guiding Bolt, affected by Otto's Irresistible Dance, Paralyzed, Petrified, Restrained, Stunned, Blinded or Unconscious. Sounds like a big list but they are all uncommon conditions. Keep an eye out for the spells on your party's caster's lists that could do this an maybe persuade them to take them.

• Attack a target after casting True Strike or after being affected by Foresight (9th level spell). True Sight takes up your action and it is rarely acceptable to sacrifice one turn's action just to get advantage on the next. Better to just attack on both turns without advantage unless there is no possible means for sneak attack.

• Attack a target a Battle Master Fighter (this can't be you) hit with the Distracting Strike maneuver.

• Attack the target after using Feinting Attack on it (if you yourself have at least 3 Battlemaster Fighter or the Martial Adept Feat).

• Attack in full darkness while you have Darkvision and your target does not.

• Attack first during a surprise round if you have the Assassin subclass.

• Attack while your Mage Hand distracts the Target using Versitle Trickster (13th level Arcane Trickster).

• Attack with Reckless Attack if you have 2 levels of Barbarian.

Archetypes

The Rogue has 5 official archetypes. There are three that emphasize utility (Arcane Trickster, Mastermind, & Thief), one the emphasizes ranged combat (Assassin), and 1 that emphasizes melee (Swashbuckler. The two combat oriented archetypes are the most common, and for good reason. Most Rogues don't need more utility and want to buff their damage potential. However, they are all fun in their own way and will all be summarized here.

Arcane Trickster

Level	Ability
3rd	Spellcasting Mage Hand Legerdemain
9th	Magical Ambush
13th	Versatile Trickster
17th	Spell Thief

Spell Casting

You are a 1/3 spellcaster. Too much info to summarize well.

Magehand Legerdemain

When casting mage hand it can be invisible. This allows you to additionally stow or retrieve objects in held creature’s containers, or pick locks and disarm traps at range.

Magical Ambush

If you are hidden from a creature when you cast a spell on it, the creature has disadvantage on any saving throw it makes against the spell this turn.

Versatile Trickster

As a bonus action you can designate a creature within 5 feet of your mage hand who you may then gain advantage against on attack rolls until the end of the turn.

Spell Theif

When a creature casts a spell that affects you, you can use your reaction to force the creature to make a saving throw with its spellcasting modifier against your spell save DC. On a failed save you negate the spell’s effect and you steal the knowledge of the spell if it is at least 1st level and of a level you can cast. You know the spell for the next 8 hours and the creature cannot cast the spell during that time. One use per long rest.

Assassin

Level	Ability
3rd	Bonus Proficiencies Assassinate
9th	Infiltration Expertise
13th	Impostor
17th	Death Strike

Bonus Proficiencies

Proficiency with disguise kit and poisoner’s kit.

Assassinate

You have advantage on attack rolls against creatures which have not yet taken a turn in combat. Also, all hits against surprised creatures are critical hits.

Infiltration Expertise

25gp and seven days prep to create false identity. Creatures require obvious reason to doubt your disguise.

Impostor

3 hours to prep ability to perfectly mimic the speech, writing, and behavior of another person. You have advantage if a wary creature suspects you.

Death Strike

Surprised creatures you attack must make a Con. save at (DC8 + your Dex. Mod. + your proficiency bonus) or take double damage of your complete attack.

Mastermind

Level	Ability
3rd	Bonus Proficiencies, Master of Intrigue Master of Tactics
9th	Insightful Manipulator
13th	Misdirection
17th	Soul of Deceit

Bonus Proficiencies:

Disguise kit, forgery kit, one gaming set of choice, two languages.

Master of Intrigue:

You can unerringly mimic the speech patterns and accent of a creature that you hear speak for at least 1 minute.

Master of Tactics:

You can use the Help action as a bonus action. When you use the Help action to aid an ally in attacking a creature, the target of that attack can be within 30 feet of you if the target can see or hear you.

Insightful Manipulator

If you spend at least 1 minute observing or interacting with another creature outside combat, the DM must tell you two of the following characteristics of your choice about the creature:

• Intelligence score
• Wisdom score
• Charisma score
• Class levels (if any) At the DM's option, you might also realize you know a piece of the creature's history or one of its personality traits, if it has any.

Misdirection

When you are targeted by an attack while a creature within 5 feet of you is granting you cover against that attack, you can use your reaction to have the attack target that creature instead of you.

Soul of Deceit

Your thoughts can't be read by telepathy or other means, unless you allow it. You can present false thoughts by making a Charisma (Deception) check contested by the mind reader's Wisdom (Insight) check. Additionally, no matter what you say, magic that would determine if you are telling the truth indicates you are being truthful, if you so choose, and you can't be compelled to tell the truth by magic

Swashbuckler

Level	Ability
3rd	Fancy Footwork Rakish Audacity
9th	Panache
13th	Elegant Maneuver
17th	Master Duelist

Fancy Footwork

If you make a melee attack against a creature on your turn, that creature cannot make opportunity attacks against you for the rest of your turn.

Rakish Audacity

You add your Charisma modifier to your initiative bonus, and you may use Sneak Attack with any melee attack made against a target that has none of your allies adjacent to it.

Panache

As an action you can make a Charisma (Persuasion) check contested by your target’s Wisdom (Insight) check. This requires effective communication. If you succeed, a hostile creature must target you and cannot move away from you for 1 minute or if you move more than 60 feet away from the target. A non-hostile creature will be charmed for 1 minute and will regard you as a friendly acquaintance.

Elegant Manuever

You can use a bonus action to gain advantage on the next Dexterity (Acrobatics) or Strength (Athletics) check you make on your turn.

Master Duelist

If you miss with an attack you can choose to roll the attack again with advantage. This cannot be used again until you finish a short or long rest.

Thief

Level	Ability
3rd	Fast Hands Second Story Work
9th	Supreme Sneak
13th	Use Magic Device
17th	Thief's Reflexes

Fast Hands

You may use cunning action to make dexterity checks to interact with thieves’ tools, disarm traps, use an object, etc.

Second Story Work

Climbing no longer costs extra movement. Running jump distance increases by number of feet equal to Dexterity modifier.

Supreme Sneak

You have advantage on Dexterity (stealth) checks if you move no more than half your speed in a turn.

Use Magic Device

You ignore all class, race, and level requirements on the use of magic items.

Thief's Reflexes

You can take two turns during the first round of any combat, the first at full initiative, the second at -10.

Rogue Fighting Options

So now you have built a solid backbone for your character to have all this out of combat utility, but at the end of the day we all want to do damage in combat. So what will it be? Ranged or melee? What weapon will you use? What spells will you try to get to aid you? What Feats do you need? This part of the guide will rank the best fighting methods in order from best to worst.

Melee: Sword & board

What you need

• Booming Blade (BB) Cantrip
• Shield Proficiency

Sword Coast Adventurer's Guide (SCAG) did a lot for the Rogue, the Swashbuckler archetype being the bees knees, but BB is a game changer for melee Rogue fighting style. Two Weapon Fighting (TWF) was and still is a fine way to get more damage as a Rogue, as well as an extra chance to land a Sneak Attack if you missed the first time. Let's take a look at why BB takes the lead.

Booming Blade

Spell	Description
Class	Sorcerer, Warlock, Wizard
Casting Time	Action
Duration	1 Round
Description	Make a melee attack with the spell. If it hits, the target takes 1d8 thunder damage if they move before the spell ends. At 5th level an extra 1d8 damage is added to the attack, and 1d8 is added if the target moves. Another 1d8 is added to both at level 11, and again at level 17.

BB requires no Feat to operate, scales with character level, and does more damage on average than TWF by level 5, and can be obtained at level 1. You can get it by four possible ways:

• High Elf Cantrip
• Half Elf who replaces Skill Versatility w/ High Elf Cantrip
• The Magic Initiate Feat
• Multiclassing into Warlock, Sorcerer, or Wizard.

Now since you are only making one attack each turn, you might as well carry a shield. The only way to do this is by multiclassing, the Fighter or Ranger being the best choices.

What you want

• Shield Master Feat
• Sentinel Feat
• Lucky Feat
• Medium Armor Master Feat
• Bonus Action Spells or Battlemaster Maneuvers

None of these are required for the build to work, but they just make it better. Shield Master lets you shove an opponent prone using your bonus action first, then you hit them with advantage BB, then you walk away. Sentinel is great for off turn Sneak Attacks. Lucky helps if you miss with your one chance to hit for damage on your turn. Bonus action spells such as Hunter's Mark, Ensnaring Strike, Hex, etc. that operate on a bonus action add damage without restricting BB. Battlemaster Maneuvers also work in tandem with BB for more damage and off turn sneak attacks.

Ranged: Heavy Crossbow

What you need

• Martial Weapon Proficiency
• Archery Fighting Style
• Mask of the Wild, Naturally Stealthy, or Skulker Feat

This will not out damage the melee Swashbuckler, but its first round burst damage will be immense. If you are enamored with being an archer this is the way to do it. Get a hiding helper feature from your Race and multiclass into Fighter or Ranger to get proficiency with the Heavy Crossbow and the archery fighting style (Range doesn't get this until level 2).

What you want

• Sharpshooter Feat
• Crossbow Expert Feat
• Extra Attack Ability
• Alert Feat
• Lucky Feat
• Bonus Action Spells or Battlemaster Maneuvers

The hardest part with this build is that you are always Feat starved. There are so many Feats that apply to ranged combat methodology. You also really want an extra attack for more damage with sharpshooter, which means taking 5 whole levels of multiclass and losing out on 2d6 Sneak Attack damage which in some ways makes it not worth it unless you can be sure about hitting the +10 from Sharpshooter. You take way more gambles with this build, but if your party has enough melee characters then this can be a fun support option.

Spells Rogues Like

Seeing as getting as many Sneak Attack's as possible is one of the Rogue tenants, spells that can be cast as bonus actions or in conjunction with weapon attacks are great additions to the Rogue skill set. To get spells that fall in this category requires multiclassing. The Rogue might also consider utility spells to help assist them outside of combat, some of which can be attained through the Arcane Trickster archetype, and others through multiclassing.

Combat Oriented Cantrips

These all benefit melee oriented Rogues, as they can be a way to gain additional damage or grant you an opportunity for Sneak Attack.

Booming Blade

Spell	Description
Class	Sorcerer, Warlock, Wizard
Casting Time	Action
Duration	1 Round
Description	Make a melee attack with the spell. If it hits, the target also takes 1d8 thunder damage if they move before the spell ends. Works beautifully for the Swashbuckler.

Green-Flame Blade

Spell	Description
Class	Sorcerer, Warlock, Wizard
Casting Time	Action
Duration	Instantaneous
Description	Make a melee attack with the spell. If it hits, and there is a creature within 5 feet of the target, you can have that creature take fire damage equal to your spell modifier.

Combat Oriented Level 1 Spells

Ensnaring Strike

Spell	Description
Class	Ranger
Casting Time	bonus action
Duration	Concentration up to 1 minute
Description	Strength save or target takes 1d6 piercing damage at the start of its turns until the spell ends or it spends an action and succeeds a strength check against your spell save DC.

Hail of Thorns

Spell	Description
Class	Ranger
Casting Time	bonus action
Duration	Concentration up to 1 minute
Description	Hit a creature with a ranged weapon attack and it along with all creatures within 5 ft must take a Dexterity saving throw. Fails take 1d10 piercing damage, successes take 1/2 damage.

Hellish Rebuke

Spell	Description
Class	Warlock
Casting Time	Reaction
Duration	Instantaneous
Description	Use reaction if you are attacked by enemy creature within 60ft. Creature must take a Dexterity saving throw. Fails take 2d10 fire damage, successes take 1/2 damage.

Hex

Spell	Description
Class	Warlock
Casting Time	bonus action
Duration	Concentration up to 1 hour
Description	Target a creature within 90 ft. Add 1d6 necrotic damage to all your weapon attacks against the creature until the spell ends, and choose an ability for the creature to have disadvantage with until the spell ends. If target drops to 0 health before the spell ends you may use bonus action to transfer it to another creature. Only remove curse can end this spell early.

Hunter's Mark

Spell	Description
Class	Ranger
Casting Time	bonus action
Duration	Concentration up to 1 hour
Description	Target a creature within 90 ft. Add 1d6 extra damage to the target whenever you hit it with a weapon attack. Additionally, you have advantage on Perception & Survival checks to find the creature. If the creature drops to zero hit points before the spell ends you may transfer the mark to another creature by using a bonus action.

Multiclassing Options

There are a multitude of multiclassing options available to the Rogue, some practical, and some hilarious although not optimized. This guide will focus on the three best options, the Bard, the Fighter, and the Warlock, which all can greatly supplement the Rogue lifestyle with little investment, and have continual payoff should you want to invest further. That said, take a look around at the other classes for options if you want to go against the grain. Rogue/Druid stealth bear anyone?

Bard

Double down on utility and get some spells. What's not to love? Well, if your party already has a bard then there is far less utility gained for the party by you taking Bard levels.

1st bard level

• 1d8 + Con HP, (same as Rogue)
• 2 Bard Cantrips, 4 Bard Spells
• 2 Level 1 Spell Slots
• Bardic Inspiration ability

Bardic Inspiration fights for your bonus action, but it can be nice now and again, especially if you remember/are able to cast it before the fighting starts. Bard spells are not so great for combat and damage, but there is a lot of utility in there, and if you are taking Bard levels combat potential is never going to be your forte.

2nd bard level

• 1d8 + Con HP, (same as Rogue)
• 1 Bard Spell
• 1 Level 1 Spell Slot
• Jack of All Trades ability
• Song of Rest ability

Jack of All Trades is a nice +1 to your non primary skills and Song of Rest can be great for those long dungeon crawls. Otherwise a pretty unremarkable level. Stick it out to level 3 Bard for the good stuff.

3rd bard level

• 1d8 + Con HP, (same as Rogue)
• 1 Bard Spell
• 1 Level 1 Spell Slot
• 2 Level 2 Spell Slots
• Expertise ability
• Bard College (Lore or Valor)

Lore Bard for Cutting Words & 3 Bonus Skill proficiences and Expertise are the biggest reason to take any Bard levels at all. Now you have double proficiency bonus in 4 total skills, and are proficient in 9, 10, or 11 total depending on race, and have 1/2 proficiency in the rest. Cutting Words gives you a reliable use of your reaction and is a nice debuff to the enemies. Don't go Valor Bard. If Valor Bard looks sweet to you, just go Fighter instead.

Fighter

Even if you don't want to multiclass at all, every Rogue who isn't running a different multiclass build should take a Fighter level, and should consider doing so early on. The Fighter class has perfect synergy with the Rogue's Sneak Attack and can greatly help your combat potential, and no DM is ever going to have a problem with you "learning how to fight better." Plus, this is the only other class the Rogue can invest in heavily and not lose out on Ability Score Increases/Feats. In fact, taking Rogue 12 / Fighter 8 you get 7 total feats, as much as a dedicated Fighter would get.

1st fighter level

• 1d10 + Con HP, more than the Rogue
• Fighting Style
• Martial Weapons, Medium Armor, & Shield proficiency
• Second Wind ability

Some extra HP and Second Wind go a long way for keeping Rogues alive (especially early on), a fighting style can help your damage/accuracy, and the equipment proficiencies can be crucial to a nice perk depending on your build. If you can afford Breastplate it will likely yield better AC total than Studded Leather unless you have increased your Dex, and if you are not dual wielding getting a shield for another +2 AC is fantastic.

2nd fighter level

• 1d10 + Con HP, more than the Rogue
• Action Surge

Admittedly not the best distraction from taking more Rogue levels, but being able to act twice in a turn when you absolutely need it can be great, especially if you pair it with the Assassin's first round ability to autocrit surprised targets. Besides that, extra health is always nice, but you want this level mostly because you are after a Fighter archetype.

3rd fighter level

• 1d10 + Con HP, more than the Rogue
• Archetype (Battle Master or Champion)

Highly lean towards Battle Master on this one because it gives you some great flexibility towards obtaining sneak attacks, hitting your attacks, and dealing extra damage. It is sad that you only have 4 to use, but keep in mind they regenerate on short rests so you can burn all 4 in nearly every fight. Champion is not bad either because critical hits double Sneak Attack damage dice as well.

4th fighter level

• 1d10 + Con HP, more than the Rogue
• Ability Score Increase or Feat

You do this unless you don't mind losing out on a feat.

5th fighter level

• 1d10 + Con HP, more than the Rogue
• Extra Attack

Every class gets awesome abilities at level 5, and if you already took 4 levels of Fighter you really should stick it out for one more level for the Extra Attack.

Multiclassing Options Continued

Warlock

The Warlock would be the easiest sell for a Rogue multiclass option if it were not for the backstory. You get a ton of goodies for just taking 1 warlock level, but depending on the nature of your DM they might insist that you take the "selling your soul for devil powers" thing seriously. Word for word from the PHB, "A warlock is defined by a pact with an otherworldly being." So even if your DM let's you have a story opportunity to find some otherworldly demon to make a pact with, your character may end up regretting their decision to, ahem, "make a deal with the devil." But hey, dem sum sweet goodies.

1st warlock level

• 1d8 + Con Mod HP, same as the Rogue
• An Otherworldly Patron ability
• Pact Magic (2 Cantrips, 2 1st level spells, 1 Spell Slot)

So first of all, the three Patron ability options are all great fun. Fey Presence lets you force a Wisdom save on all creatures in a 10ft cube to be either charmed or frightened, your choice. Fun, although it takes your action, so probably the least appealing option. Dark One's Blessing lets you gain temporary HP when you kill something up to your Cha Mod + Warlock level. So some extra HP basically. Everyone likes that. Awakened Mind lets you communicate telepathically with creatures you see within 30 ft. This one can be incredibly useful for a Rogue who is sneaking ahead of the party, and wants to communicate a plan to the party without leaving position or making sound. Huge really.

But the real reason you came here is for the spells, specifically Hex and Booming Blade. Good god the spells. Take Booming Blade, Green-Flame Blade, Armor of Agathys and Hex. Hex casts as a bonus action, you get an extra 1d6 damage on every attack you make against the target creature, you can move it around with a bonus action, and it works in conjunction with damage Cantrips. It's like trading a sneak attack damage dice to be more guaranteed and if you only take 1 level ultimately you don't lose any sneak attack dice in the end game. Extra points if you get multiple attacks later on or dual wield for even more damage from it. Also, taking the Eldritch Blast Cantrip is never a bad idea because sometimes when you can't get sneak attack, especially at higher levels, it will be an a good fallback attack option with respectable damage.

Plus, Booming Blade in conjunction with Swashbuckler builds can be super cheeky. Hit the enemy, run away for free with no fear of opportunity attack, and if they move they take damage. Plus at higher levels you get to add damage to the attack. Epic. And don't forget that Warlock Spells regenerate on short rests, so even though you only have one spell slot for Hex, you will still be likely to have access to it in most fights.

The only problem is that if you want to go two weapon fighting or get extra attacks through Fighter or something you can't attack twice with Booming Blade. However, the damage to Booming Blade scales with your character level, not Warlock level, so by character level 5 you have slightly less than the damage equivalent of an extra attack being added to your attack.

2nd warlock level

• 1d8 + Con Mod HP, same as the Rogue
• 2 Eldritch Invocations
• 1 more spell slot and 1 more level 1 spell

Same HP as Rogue, and an extra spell slot means you can finally cast the other spells you took because before Hex will always take priority of your spell slot. Not bad, but the Eldritch Invocations are where it's at. Devil's Sight is a fantastic choice for Human's which gives you better darkvision than any race get's standard. Hell it even works in magical darkness. Just get someone to cast darkness around you and get sneak attacks for days. Beguiling influence is great for more skill proficiencies, although you have to forgo them as your base picks, and Eyes of the Rune Keeper for reading all writing can be super handy. Then there is Mask of Many Faces for casting Disguise Self at will... the list goes on. Hopefully you are beginning to see why Roguelock is such a powerful combo.

3rd warlock level

• 1d8 + Con Mod HP, same as the Rogue
• 1 more spell and your spells are level 2 now
• Pact Boon

To be honest this is the least necessary. Most level 2 Warlock spells consume your action which is bad, but hey, you can get the Darkness spell and cast it yourself for sneakiness. The Pact Boons are sweet though if you want a familiar, a magical weapon that you can draw out of nowhere (this is a great way to start doing magic damage and ignore those annoying resistances some monsters have), or get some extra Cantrips from any of the other classes. Not quite as pivotal as the first 2 Warlock levels, but there is enough reason to do it. It's not really worth it to go any farther down warlock if you want to focus on your Rogue lifestyle though.

Assassin Build

This build focuses on one primary objective, which is to deal one high damage sneak attack shot from range every round with advantage.

Setup

Race: Wood elf

This is a contest between the Variant Human’s bonus Feat and the Wood Elf’s extra ability point, extra movement, darkvision, fey ancestry, trance, and mask of the wild.

Background: Spy

Trade Thieves' Tools for a bonus language and the Gaming set for forgery kit.

Class: Rogue

This build will multiclass into fighter to enhance archery skills.

Ability Scores

Ability	Score
Strength	08 ( 08 + 0 )
Dexterity	16 ( 14 + 2 )
Constitution	12 ( 12 + 0 )
Intelligence	10 ( 10 + 0 )
Wisdom	16 ( 15 + 1 )
Charisma	13 ( 13 + 0 )

Dexterity is number one as with most rogue builds, Wisdom is second for perception mostly but also insight and survival, Charisma is next so that you can be personable, Constitution is fourth because it can't be ignored, Intelligence isn't dumped completely only because you need investigation, and strength is of course dumped. If you can get someone else to take care of investigation then dump Intelligence and get more Charisma.

Skills

Acrobatics, Deception, Insight, Investigation, Perception, Persuasion, Stealth

Acrobatics is for getting into positions, but some might want Sleight of Hand instead. Drop Investigation first if someone else can do it, but remember this is how you are finding traps, which is kinda your role by default.

Equipment

Rapier, Longbow, Studded Leather Armor

Level 1: Rogue 1

Take Expertise on Stealth & Perception. Right out the door you are pretty sneaky and dishing out 1d8+3 hits with 1d6 sneak attack damage, which is pretty high this early in the game. The only people beating you in damage are builds like dual wielding variant human fighter which starts the game with 1d8+3 twice. Just remember that outside of combat you are going to be a lot more useful than that fighter.

Level 2: Rogue 2

You need Cunning Action more than any other build so that you can attempt to hide as a bonus action to setup the next round’s sneak attack.

Level 3: Rogue 2 / Fighter 1

It’s time to take a fighter dip for martial weapon proficiency which means you can use the heavy crossbow, and the Archery Fighting Style for increased shot accuracy, which at the end of the day is everything for this build. Also some extra HP, and Second Wind make you a hell of a lot more durable at these low levels. You should still avoid taking hits though.

Level 4: Rogue 3 / Fighter 1

Time to increase sneak attack damage and start the ASSASSIN archetype for crazy first round damage and completing your accessory kit options. On a surprise round you deal [(1d10+3) + 2d6]x2 assassinate damage.

Level 5: Rogue 4 / Fighter 1

By this point we are begging for a feat, and it is a tough choice. Taking the SHARPSHOOTER feat will make your sniping even better, but ALERT would help ensure you get the most out of Assassinate and prevent enemies from using your own tactics against them. Sharpshooter wins here because it has more effect over the course of the fight, and ignoring cover while shooting at insane range is excellent.

Level 6: Rogue 4 / Fighter 2

Action surge and more HP are nice, but your goal lies at the next level. Use action surge on your surprise round to get another free critical hit. No extra Sneak Attack damage though.

Level 7: Rogue 4 / Fighter 3

BATTLEMASTER TIME. Take precision attack, riposte, and trip attack as your maneuvers. Thanks to precision shot and hopefully your own knowledge in gaining shot advantage you will rarely miss, trip attack is great for adding extra shot damage and slowing enemies down, and riposte gives you the opportunity to use your reaction for damage, and sneak attack damage at that if you are set up for it.

Level 8: Rogue 4 / Fighter 4

Take the Alert feat. Going first is important for your archetype feature and prevents enemies from using your own tactic against you.

Level 9 & Beyond

Take another level of Fighter next for the extra attack and then a Rogue Level for Uncanny Dodge and more sneak attack damage. At this point just choose more levels in either as you please. You have all the necessary Feats for the build to function well so take two Ability score increases to get Dexterity to 20. The Lucky Feat is also a great choice for you to help prevent your shots from screwing up and saving you in a pinch.

Mastermind Build

This is going to take the term "skill monkey" and just go absolutely ham with it. In combat your focus will be buffing your allies while dishing out a sneak attack here and there, while out of combat you will be able to do nearly everything. This build can be tough to start, the fun won't start until level 3, and you will be incredibly fragile as a whole. This build is not recommended for new players.

Setup

Race: half elf

The ability scores and skill proficiencies are what you care about. Lightfoot Halfling to RP Tyrion Lannister is compelling, but the Half Elf has more of what this build needs.

Background: Courtier

Everything is perfect with this. You don't have to change anything.

Class: Rogue

This build will multiclass into bard to add extra utility.

Ability Scores

Ability	Score
Strength	08 ( 08 + 0 )
Dexterity	13 ( 13 + 0 )
Constitution	08 ( 08 + 0 )
Intelligence	16 ( 15 + 1 )
Wisdom	14 ( 13 + 1 )
Charisma	16 ( 14 + 2 )

Strength, Constitution, and even Dexterity take a back seat in this build while Intelligence, Wisdom, and Charisma are maxed.

Skills

Deception, Insight, Investigation, Perception, Persuasion, Sleight of Hand, Stealth, Survival

Equipment

Rapier, Light Crossbow, Studded Leather Armor

Level 1: Rogue 1

Starting off the bat you are already a great skill monkey. Take Expertise in Persuasion and Deception and you have +7 to your main Charisma skills and know 5 languages, which means talking to people is going to go pretty well. If anything goes wrong, it will likely be because your less than tact compatriots have fumbled your plan. When it comes to combat just hide in the back and shoot things with your crossbow.

Level 2: Rogue 2

You now have cunning action, thank god. Using it wisely should help prevent you from dying greatly by allowing you to manage your distance.

Level 3: Mastermind 3

You know have proficiency in all the relevant kits for trickery and espionage, and you have a grand total of 7 languages. 7. That's enough for all the standard languages bar one, and with Master of Intrigue you can talk like the locals perfectly. But the best part is Master of Tactics. Now not only are you shooting somebody with a crossbow every turn, hopefully with sneak attack, but you are giving your fighter advantage on his first attack roll every round.

Level 4: Mastermind 3 / Bard 1

It's time to pickup some utility spells, another skill proficiency, and Bardic Inspiration (BI) for extra help. Now yes, BI is going to be fighting with MoT for your bonus action, but this won't be a problem after level 6, and you can just preemptively give people BI before you think a fight will start.

Level 5: Mastermind 3 / Bard 2

Jack of All Trades is a nice boost to your non-proficient stats and Song of Rest can be very useful during long dungeon crawls.

Level 6: Mastermind 3 / Lore Bard 3

This is what the dip into bard was for. A second dose of Expertise and 3 extra skill proficiencies, combined with your progress so far means you are double proficient in 4 skills, proficient in 8, and +1 in all the rest. Between you and the rest of the party all 18 skills should be covered by now. But the best part is Cutting Words, which is now your primary use of BI and a secure way to make use of a reaction. Now every turn in combat you are making a sneak attack hopefully, giving a friend advantage, and applying a nice debuff on the enemy.

Level 7: Mastermind 4 / Lore Bard 3

It's feat time. You could take Skilled and get even more skill bonuses, Alert if you want to prevent the enemy from getting the drop on you, or Observant if you really want to make the DM pull his hair out because you keep spotting things he was trying to hide without even trying.

Level 8: Mastermind 4 / Lore Bard 4

One feat was nice. Let's get another.

Level 9 & Beyond

Just keep increasing Mastermind at this point. Or bard if you prefer. If you are feeling too squishy, take a level in Knowledge Cleric which gives you even more expertise skills, more languages, medium armor, and shields. This could be inserted at level 2 even.

Swashbuckler Build

Versatility is the name of the game, and the Swashbuckler has it in spades. The best party face money can buy and the highest damage dealer a Rogue can hope to be.

Setup

Race: Half Elf

Trade the Skill Versatility trait for the High Elf Cantrip option and take Booming Blade.

Background: Courtier

Everything is perfect with this. You don't have to change anything.

Class: Rogue

This build will multiclass into fighter to enhance dual wielding skills.

Ability Scores

Ability	Score
Strength	08 ( 08 + 0 )
Dexterity	16 ( 15 + 1 )
Constitution	14 ( 13 + 1 )
Intelligence	10 ( 10 + 0 )
Wisdom	12 ( 12 + 0 )
Charisma	16 ( 14 + 2 )

Dexterity and Charisma are the most important, nice Constitution for Health, a touch of Wisdom to help out, Intelligence is strictly average, and Strength as usual is dumped.

Skills

Deception, Insight, Investigation, Perception, Persuasion, Stealth

Equipment

Rapier, Light Crossbow, Studded Leather Armor

Level 1: Rogue 1

Take Expertise on Stealth & Persuasion. Your good looks can get you the influence and information you need, and when the fight starts you have options. You have 15 AC which is the standard for level 1 Rogue, and you are dealing (1d8 + 3) + (1d6) + (1d8) if you get a sneak attack and the target moves. Those are two ifs for now but they will be near guaranteed later.

Level 2: Rogue 2

You need to become a Swashbuckler ASAP. Cunning Action is going to be useful for Dash to get you where you need to be.

Level 3: Rogue 3

The Swashbuckler gets the best first Archetype feature by far. You now have +6 to initiative, you don’t need Cunning Action for disengage most of the time thanks to fancy footwork, and you can get sneak attacks all by yourself against single opponents. It will be incredibly uncommon for you to not have a sneak attack opportunity. Awesome.

Level 4: Rogue 3 / Fighter 1

You want shield proficiency and you should be able to buy breastplate which will bring your total AC to 18 with the shield. Take the Dueling Fighting style for extra damage. You also get some extra health and Second Wind which seriously helps you stay alive. The build is now fully functional.

Level 5: Rogue 4 / Fighter 1

Tough choice here. Increase Dexterity to 18, or take Shield Master, Medium Armor Master, Lucky, or Sentinel Feat. All good options. Increase Dex to 18 is arguably the best (+1 attack bonus, +1 damage, +1 Dex Save, +1 Acrobatics, Sleight of Hand, Stealth). You can also get 18 AC with light armor so no need for breastplate. Oh, also don't forget that BB just got huge.

Level 6: Rogue 5 / Fighter 1

You are in melee enough that you are going to have to take some damage. Why not take half with Uncanny Dodge? Also more Sneak Attack damage is nice. You now deal (1d8 + 4 ) + (3d6) + (1d8) on Sneak attack and if the target moves you get an extra (2d8). Excellent.

Level 7: Rogue 5 / Fighter 2

Oh yeah, we want that Battlemaster archetype, but hey Action Surge will do for now for even more damage when you need it.

Level 8: Rogue 5 / Fighter 3

BATTLEMASTER TIME. Take precision attack, riposte, and trip attack as your maneuvers. Precision shot can be really nice if getting the hit is crucial. Trip attack is awesome for extra damage, setting up your friends for advantage attacks, The best one of all, Riposte, gives you the opportunity to use your reaction for damage, and sneak attack damage at that if you are set up for it. Between this and Uncanny Dodge you always have an opportunity to use your reaction in a meaningful way should anyone attempt to attack you. You now have mastered the 5E action economy.

Level 9 & Beyond

Depends what you feel your build is lacking at this point. You should consider another Fighter level so you can max out Dex at 20. The rest is up to you.

Roguelock Build

Trading your soul for strong offensive magic and paring it with sneaky maneuvers for great effect.

Setup

Race: Half Elf

Charisma is the Warlocks spellcasting modifier, so as per the usual mantra, unless you are dumping Charisma, Half Elf is the way to go.

Background: Outlander or Urchin

Change up a couple options and this could work well both with backstory and ability wise. Easy to spin how an Outlander or Urchin would be willing to make a deal with the devil in exchange for magic powers so to speak.

Class: Rogue

This build will be multiclassing into Warlock, and it is very tempting to actually start as a Warlock then switch to Rogue for thematic reasons, but you will lose out on a skill proficiency and will not have the Rogue's weapon proficiencies. As far as feature gains go, Rogue to Warlock is straight better than Warlock to Rogue. However for RP reasons it might be easier to start as a Warlock and switch to Rogue. Talk to your DM on this one.

Ability Scores

Ability	Score
Strength	08 ( 08 + 0 )
Dexterity	16 ( 15 + 1 )
Constitution	14 ( 13 + 1 )
Intelligence	10 ( 10 + 0 )
Wisdom	12 ( 12 + 0 )
Charisma	16 ( 14 + 2 )

Dexterity and Charisma are the most important, nice Constitution for Health, a touch of Wisdom to help out, Intelligence is strictly average, and Strength as usual is dumped.

Skills

Acrobatics, Deception, Insight, Investigation, Perception, Persuasion, Stealth, Sleight of Hand

Equipment

Rapier, Light Crossbow, Studded Leather Armor

Level 1: Rogue 1

Take Expertise on Stealth & Persuasion. Your good looks can get you the influence and information you need, and when the fight starts you have options. You have nothing really special in combat yet, but 1d8+3 + 1d6 damage a turn with sneak attack is not bad at all.

Level 2: Rogue 1 / Warlock 1

You wield a wand in one hand and a rapier in the other. All of the Pact Magic options are great, but The Great Old one is encouraged so you can be stealthy and still impart battle tactics to the party. For your spells take Eldritch blast, Booming Blade, Hex, and Hellish Rebuke. You won't get any chances to use Hellish Rebuke for now because you will be to busy using your 1 slot for Hex. So now with SA, Hex, and BB you are dealing (1d8 + 3) + (1d6) + (1d6) a turn and you if the target moves it takes another 1d8. Epic. Also you have Eldritch blast as a great way to deal damage if everything goes wrong.

Level 3: Rogue 1 / Warlock 2

An extra slot is nice for flexibility, pick up Charm Person or something for an extra spell as well. The biggest reason for this is for Eldritch invocations, specifically Devil's Sight. You can see 120ft normally in darkness, even magical darkness. That is even better than superior darkvision racial traits that have drawbacks. Perfect for the token stealthy party member. Lot's of good options for the second choice, but Agonizing Blast should be the go to choice, as it now makes Eldritch blast do significantly more damage now, and at higher levels, meaning you will always have a reliable source of damage.

Level 4: Rogue 2 / Warlock 2

This level choice hinges on how badly you want to use the darkness spell in conjunction with your Devil's sight for endless sneak attacks. If your party has someone else who can get this spell beg and plead them to do it. If they can't/won't, take another Warlock level and get it yourself. So back to the Rogue, you get Cunning Action now, which you have been sorely missing.

Level 5: Rogue 3 / Warlock 2

Finally time for an archetype and more sneak attack damage. This build will be using Swashbuckler, but Assassin is a viable option as well. Now you can dance around like the mad crazed swordsman you are. Booming Blade is dealing 1d8 damage extra now on hit, and you can use Fancy Footwork to disengage for free, leaving them stuck to either sit there or take 2d8 damage. With Hex and Sneak Attack you are hitting for (1d8 + 3) + (2d6) + (1d6) +(1d8). Also don't forget that Eldritch Blast is now (1d10+3)x2 if you need it.

Level 6: Rogue 4 / Warlock 2

Time for a feat. Lots of good options, but you want War Caster to make sure you don't drop Hex and can use your reaction to attack with Eldritch Blast. Also now you can tech into dual wielding or get a shield later if you want. Dual wielding is not worth it to you without the feat because moving Hex around consumes your bonus action.

Level 7 & Beyond

Depends what you feel your build is lacking at this point. Want more AC and damage? Take some Fighter levels. More spells and you feel like sealing the deal with your pact dude? Take more Warlock. Want to stick to Rogue the rest of the way? That's good too.